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光诱导铜催化的烯丙基和炔丙基碳氢键对映选择性胺化反应。

Photoinduced copper-catalysed enantioselective amination of allylic and propargylic C-H bonds.

作者信息

Dai Ling, Chen Ying-Ying, Wang Jing-Jun, Chen Jun-Jia, Zhou Qi-Lin

机构信息

State Key Laboratory and Institute of Elemento-Organic Chemistry, College of Chemistry, Frontiers Science Center for New Organic Matter, Nankai University Tianjin 300071 China

出版信息

Chem Sci. 2025 Apr 17;16(21):9213-9219. doi: 10.1039/d5sc00872g. eCollection 2025 May 28.

Abstract

The hydrogen atom transfer (HAT)-mediated strategy has emerged as a straightforward and powerful approach for oxidative C-H bond functionalization. However, despite remarkable progress in this field, enantioselective allylic and propargylic C-H aminations remain a challenge. In this study, we developed highly enantioselective allylic and propargylic C-H aminations by combining a visible light-activated HAT process with copper catalysis. Using this method, a wide range of alkenes and alkynes can be converted into high-value chiral allylic and propargylic amines with high enantio-, regio-, and /-selectivity. These enantio-enriched amines serve as versatile building blocks in organic synthesis and hold significant potential for applications in the synthesis of pharmaceuticals, natural products and other bioactive molecules.

摘要

氢原子转移(HAT)介导的策略已成为氧化C-H键官能化的一种直接且强大的方法。然而,尽管该领域取得了显著进展,但对映选择性烯丙基和炔丙基C-H胺化仍然是一个挑战。在本研究中,我们通过将可见光活化的HAT过程与铜催化相结合,开发了高度对映选择性的烯丙基和炔丙基C-H胺化反应。使用这种方法,多种烯烃和炔烃可以转化为具有高对映、区域和立体选择性的高价值手性烯丙基和炔丙基胺。这些对映体富集的胺在有机合成中作为通用的结构单元,在药物、天然产物和其他生物活性分子的合成中具有巨大的应用潜力。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0dff/12118140/e33d06199592/d5sc00872g-s1.jpg

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